Sodium Carbonate → HCID 23653918, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-bromo-2-(5,6-dimethoxy-benzoimidazol-1-yl)-thiazole-5-carboxylic acid methyl ester (40 mg, 0.1 mmol), 4-methylphenylboronic acid (20.4 mg, 0.15 mmol) in ethylene glycol dimethyl ether (1 ml) was added Na2CO3 (2M, 100 μL, 0.2 mmol) and [1,1′-bis(diphenylphosphino)-ferrocene]dichloro palladium(II) (4 mg, 0.005 mmol). The mixture was heated to 100° C. for 3 hrs. The solvent was evaporated and 2 ml water was added. It was then extracted with 2×3 ml EtOAc. The combined organics were concentrated in vacuo. To this crude was added THF (0.5 ml), water (0.5 ml), methanol (0.2 ml) and NaOH (20 mg, 0.05 mmol). The mixture was heated to 60° C. for 3 hrs. The solvents were evaporated and the crude was purified by prep-HPLC to afford 2-(5,6-Dimethoxy-benzoimidazol-1-yl)-4-p-tolyl-thiazole-5-carboxylic acid (21.1 mg, 53%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 13.57 (br.s., 1H); 8.82 (s, 1 H); 7.83 (m, 3 H); 7.39 (s, 1 H); 7.31 (d, 2 H); 3.86 (s, 3 H); 3.85(s, 3 H), 2.39 (s, 3H). MS m/z 396 (M+1).

Provenance & Evidence